Patent GB-543256-A (GB)
Title: Bisthioammeline polyalkylene ether condensation products
IPC: C08G12/30
Filed: 1940-07-11
Abstract: 543,256. Resinous condensation products ; compound sheet materials; treating textiles. RESINOUS PRODUCTS & CHEMICAL CO. July 11, 1940, No. 11571. Convention date, Sept. 30, 1939. [Classes 2 (iii) and 15 (ii)] [Also in Group VIII] Resinous condensation products are prepared by heating together, in the presence of a solvent, and under substantially neutral conditions or in the presence of an acid type catalyst, an aldehyde and a bisthioammeline polyalkylene ether of the kind described in Specification 541,025. These ethers have the general formula :- wherein A represents a lower alkylene group of two to four carbon atoms and N represents an integer from one to five inclusive. Specified aldehydes are formaldehyde, acetaldehyde, butyraldehyde, benzaldehyde and furfuraldehyde, and prefrably four to eight mols. of the aldehyde to each mol. of the ether, are employed. When an alcohol is used as the solvent, it acts also as a component in the condensation. Excess of aldehyde may be eliminated from the final product by adding to the re-action mixture methylol-forming compounds such as urea, thiourea, dicyandiamide, amides, triazines, or phenol, and co-condensed resins are thus obtained. The resinous condensates of the present invention may be incorporated with other resinous materials such as urea-formaldehyde, phenol-formaldehyde, aniline-formaldehyde and sulphonamide-aldehyde resins, furfural resins and alkyd resins, and other specified optional additions are wood flour, cotton, alpha cellulose floc, zinc stearate, starch, flour, pigments, dyes, metal powders, asbestos, chalk, clay, barytes and infusorial earth. Specified plasticizers which may be added are oil-modified alkyd resins, dibutyl sebacate, dibutyl phthalate diethoxydiethyl phthalate, and the condensates of carboxylic acids with nitro-aliphatic alcohols. Examples are given of the preparation of resinous condensates from : (1) ##<SP>1</SP>-bisthioammeline diethylether, formaldehyde and alcohol, with or without urea ; (2) ##<SP>1</SP>-bisthioammeline dietbylether, paraformaldehyde and butanol ; (3) formaldehyde and a bisthioammeline polyalkylene ether obtained by re-acting two mols. of thioammeline and one mol. of dichlorotriethylene glycol ; (4) formaldehyde and the re-action product of thioammeline with dibromtetraethylene glycol. The condensates may be further condensed or polymerized and hardened under the influence of heat and preferably in the presence of an acid catalyst, or they may be used to saturate fillers, the dried products being ground and used as moulding powders. Fibrous sheets may be impregnated with solutions of the condensates, excess solvent removed, and several of the treated sheets subjected to heat and pressure to produce a composite laminated material. In an example, an alcoholic solution of an aldehyde-bisthioammeline polyalkylene ether condensate is used to impregnate a paper sheet which is then dried and placed over a layer of wood, which is in turn placed on a sheet of paper impregnated with a phenol-formaldehyde resin and a sheet of pressed fibre board. Tnis assembly is subjected to heat and pressure'to produce a laminated product. Adhesives may be prepared from the condensates of the present invention by adding wheat flour, and a solution of ammonium thiocyanate, and such adhesives may be used in the production of plywood. Fabrics may be waterproofed and made resistant to crushing, creasing and laddering, by treatment with the condensates. Coating compositions may be prepared from the condensates, and specified additions, for this purpose, are alkyd resins, phenol-formaldehyde resins, nitrocellulose, castor oil, tricresyl phosphate, cadmium selenide, cement or plaster, and titanium dioxide.